Dichloromethane → 2-Ethynyl-4-methyl-phenol

HRID 13231

Reaktionsgleichung

Reaktionsgleichung von HRID 13231
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].C[Si]([C:14]#[CH:15])(C)C.[F-].[K+].C(Cl)Cl>CCN(CC)CC.O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[C:14]([C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9])#[CH:15]

Komponenten

8

Edukt 4

HCID 6344DichloromethaneHCID 231092-Bromo-4-methylphenolHCID 66111TrimethylsilylacetyleneHCID 522689Potassium Fluoride

Produkt 1

HCID 104868922-Ethynyl-4-methyl-phenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 68453242HCID 68453242, VerbindungLösungsmittel

Versuchsvorschrift

A flask is flushed with N2 and charged with 2-Bromo-4-methylphenol (20 mmol) and dissolved in 1/1 Et3N/dioxane. Bis(triphenylphosphine)palladium(II) dichloride (PdCl2(PPh3)2) (0.2 mmol) is added, followed by 0.4 mmol of CuI. Trimethylsilylacetylene (24 mmol) is added drop-wise to the reaction mixture. The reaction mixture is stirred overnight under N2. The solvents are removed under vacuum and the resulting liquid is extracted by washing with ethyl ether. The ethyl ether extracts are combined and washed with H2O, then dried over anhydrous sodium sulfate. The solvent was removed under vacuum and the product is purified by column chromatography. The purified product is placed in a N2-flushed flask and dissolved in methanol. Potassium fluoride (65 mmol) is added and the reaction stirred under a N2 blanket for 16 h. The reaction mixture is poured into CH2Cl2 and extracted with H2O, then dried over Na2SO4, filtered and the solvent is removed under vacuum. The resulting product is purified by column chromatography to yield 2-ethynyl-4-methyl-phenol (3).

Aufarbeitung

  1. customA flask is flushed with N2
  2. customThe solvents are removed under vacuum
  3. extractionthe resulting liquid is extracted
  4. washby washing with ethyl ether
  5. washwashed with H2O
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under vacuum
  8. customthe product is purified by column chromatography
  9. customflushed flask
  10. dissolutiondissolved in methanol
  11. stirringthe reaction stirred under a N2 blanket for 16 h
  12. extractionextracted with H2O
  13. dry with materialdried over Na2SO4
  14. filtrationfiltered
  15. customthe solvent is removed under vacuum
  16. customThe resulting product is purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-05b116f3a02a429f932af61225491e18
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728051B2

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